Editing Mesitylene (section)

==History==
Mesitylene was first prepared in 1837 by [[Robert Kane (chemist)|Robert Kane]], an Irish chemist, by heating acetone with concentrated sulfuric acid.<ref>Robert Kane (1839) [https://archive.org/details/bub_gb_AuIcAQAAMAAJ/page/n589 <!-- pg=99 --> "On a series of combinations derived from pyroacetic spirit] [acetone]" ''Transactions of the Royal Irish Academy'', vol. 18, pages 99–125.</ref> He named his new substance "mesitylene" because the German chemist [[Carl Reichenbach]] had named acetone "mesit" (from the Greek μεσίτης, the mediator),<ref>Reichenbach's research is excerpted in: C. Reichenbach (1834) [https://books.google.com/books?id=P0s9AAAAcAAJ&pg=PA298 "Ueber Mesit (Essiggeist) und Holzgeist"] (On mesit (spirit of vinegar) and wood spirits), ''Annalen der Pharmacie'', vol. 10, no. 3, pages 298–314.</ref> and Kane believed that his reaction had dehydrated mesit, converting it to an [[alkene]], "mesitylene".<ref>For an explanation of the original of the name "mesitylene", see also: Henry E. Roscoe, ''A Treatise on Chemistry'' (New York, New York: D. Appleton and Co., 1889), vol. III, [https://archive.org/details/bub_gb_atXNAAAAMAAJ/page/n110 page 102], footnote 2.</ref> However, Kane's determination of the chemical composition ("empirical formula") of mesitylene was incorrect. The correct empirical formula was provided by [[August Wilhelm von Hofmann|August W. von Hofmann]] in 1849.<ref>A.W. Hofmann (1849) "On the composition of mesitilole [mesitylene], and some of its derivatives", ''The Quarterly Journal of the Chemical Society of London'', vol. 2, [https://books.google.com/books?id=oKAwAAAAYAAJ&pg=PA104 pages 104–115]. (Note: The empirical formula of mesitylene as stated in Hofmann's paper (C<sub>18</sub>H<sub>12</sub> ) is incorrect; however, this happened because Hofmann used 6 as the atomic weight of carbon, instead of the correct atomic weight of 12. Once the correct atomic weight is used in Hofmann's calculations, his results give the correct empirical formula of C<sub>9</sub>H<sub>12</sub>.)</ref> In 1866 [[Adolf von Baeyer]] gave a correct mesitylene's empirical formula; however, with a wrong structure of tetracyclo[3.1.1.1<sup>1,</sup>3.1<sup>3,5</sup>]nonane.<ref>Adolf von Baeyer (1866) [https://books.google.com/books?id=yYlKAAAAYAAJ&pg=RA1-PA297 "Ueber die Condensationsproducte des Acetons"] (On condensation products of acetone), ''Annalen der Chemie und Pharmacie'', vol. 140, pages 297–306.</ref> A conclusive proof that mesitylene was trimethylbenzene was provided by [[Albert Ladenburg]] in 1874; however, assuming wrong benzene structure of [[prismane]].<ref>Albert Ladenburg (1874) "Ueber das Mesitylen" (On mesitylene), ''Berichte der deutschen chemischen Gesellschaft'', vol. 7, pages 1133–1137. {{doi| 10.1002/cber.18740070261}}</ref>
<gallery mode="packed" heights=120 caption="Historical mesitylene structures" class="skin-invert-image">
File:Mesitylen by Adolf von Baeyer.png|Mesitylene by Adolf von Baeyer (tetracyclo[3.1.1.1<sup>1,</sup>3.1<sup>3,5</sup>]nonane)
File:Mesitylen by Albert Ladenburg.png|Mesitylene by Albert Ladenburg (1,2,6-trimethylprismane)
</gallery>